Transition-Metal-Free Thioboration of Terminal Alkynes

被引:0
|
作者
Matsuyama, Taro [1 ]
Ishida, Hiroshi [1 ]
Wang, Chao [2 ]
Miyamoto, Kazunori [1 ,3 ]
Nakajima, Masaya [1 ]
Toriumi, Naoyuki [1 ]
Nagashima, Yuki [1 ]
Uchiyama, Masanobu [1 ,4 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan
[2] Kanazawa Univ, Fac Pharmaceut Sci, Inst Med Pharmaceut & Hlth Sci, Kanazawa, Ishikawa 9201192, Japan
[3] Keio Univ, Fac Pharm, Tokyo 1058512, Japan
[4] Shinshu Univ, Res Initiat Supramat RISM, Ueda, Nagano 3868567, Japan
来源
JACS AU | 2024年
关键词
thioboration; elementoboration; vinyl sulfide; vinyl boron; dual functionalization; alkyne; UNSATURATED-COMPOUNDS; ALLIED REACTIONS; VINYL SULFIDES; PALLADIUM; HYDROBORATION; HALOBORATION; SILABORATION; DIBORATION; CATALYSIS; OLEFINS;
D O I
10.1021/jacsau.4c00907
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We present a new type of elementoboration reaction, the thioboration of terminal alkynes. This method enables highly controllable regio-/stereo-/chemoselective cis- and trans-thioboration on demand, affording synthetically versatile and densely functionalized vinyl boron/vinyl sulfide derivatives in a straightforward manner without the need for a transition-metal catalyst.
引用
收藏
页数:7
相关论文
共 50 条
  • [1] Transition-metal-free hydroboration of terminal alkynes activated by base
    Hong, Shibin
    Zhang, Wei
    Liu, Mengyan
    Yao, Zi-Jian
    Deng, Wei
    TETRAHEDRON LETTERS, 2016, 57 (01) : 1 - 4
  • [2] Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes
    Yatabe, Takafumi
    Mizuno, Noritaka
    Yamaguchi, Kazuya
    ACS CATALYSIS, 2018, 8 (12): : 11564 - 11569
  • [3] Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration
    Abed, Hassen Bel
    Blum, Suzanne A.
    ORGANIC LETTERS, 2018, 20 (21) : 6673 - 6677
  • [4] Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes
    Matcha, Kiran
    Antonchick, Andrey P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (2-3) : 309 - 312
  • [5] Transition-Metal-Free Borylation of Alkynes and Alkenes
    Deng, Chun M.
    Ma, Yi F.
    Wen, Yan M.
    CHEMISTRYSELECT, 2018, 3 (04): : 1202 - 1204
  • [6] Transition-Metal-Free Synthesis of Alkynylphosphine Oxides from Terminal Alkynes and Chlorodiphenylphosphine Oxide
    Chen, Jianyang
    Yun, Hui
    Fu, Hongmei
    He, Huamei
    Duan, Shicheng
    Li, Mingyang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (12)
  • [7] Transition-Metal-Free Intermolecular Chlorodifluoromethylthiolation of Alkenes and Alkynes
    Yuan, Wan-Qiang
    Guo, Li-Yun
    Liu, Yu-Tao
    Li, Qing
    Shi, Jie
    Pan, Fei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) : 5981 - 5984
  • [8] Transition-Metal-Free Terminal Alkyne Addition to Isatins
    Dhara, Kalyan
    Kapat, Ajoy
    Ghosh, Tridev
    Dash, Jyotirmayee
    SYNTHESIS-STUTTGART, 2016, 48 (23): : 4260 - 4268
  • [9] One-pot transition-metal-free synthesis of alkynes and enynes
    Gu, Yuanyun
    Wu, Yu
    Wang, Yan-En
    Phadnis, Nidheesh
    Xiong, Dan
    Mao, Jianyou
    Walsh, Patrick J.
    CELL REPORTS PHYSICAL SCIENCE, 2024, 5 (08):
  • [10] Transition-metal-free hydroamination/defluorination/cyclization of perfluoroalkyl alkynes with amidines
    Sun, Li-Wen
    Yu, Zi-Lun
    Luo, Xin-Long
    Ma, Mengtao
    Shen, Zhi-Liang
    Chu, Xue-Qiang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 9 (01): : 109 - 116